For many families, a vacation property is more than just an asset – it is a symbol of family identity, tradition, and a sense of belonging. Where laughter echoes across the lake, generations learn to play games, and cherished memories are woven into weathered dock chairs.
But what happens to the family vacation property when the parents are no longer around to keep the peace?
A recent court case caught our attention: a dispute between siblings over their late mother’s cottage led to a forced sale, ending decades of shared memories. It was a harsh reminder that without a thoughtful plan, even the most treasured retreats can become battlegrounds. As Family Wealth Advisors at Barometer Capital, we have seen firsthand how quickly things unravel when succession planning is overlooked – especially when vacation properties are involved.
Source: Investment Executive, July 2025
The emotional weight of owning a vacation property with a sibling
Vacation properties carry deep-rooted emotions. In the case of two siblings, one may have deep sentimental ties; they spent every summer there, learned to swim off the dock, and brought their children to visit. Another may live in a different province, visit infrequently, and see more value in the proceeds of a sale than in ownership.
Now layer in financial dynamics. One sibling may be in a position to cover the costs of maintenance, taxes, and renovations. Another may not. Is it “fair” to leave the property equally to all children?
What happens when the roof needs replacing, the dock falls into disrepair, or one sibling cannot, or chooses not to, contribute? How are decisions made? How are weeks shared? These types of situations can foster resentment. Families who never thought they would be in court may face broken relationships and lose a cherished legacy.
Common pitfalls of vacation property succession
We regularly see the following issues when a plan is not in place:
- Unspoken assumptions about who wants or who should receive the property
- Equal ownership without equal ability to contribute
- No shared agreement on how the property will be used, maintained, or repaired
- No clear exit strategy or buyout mechanism for siblings who want out
- No plan to fund capital gains tax or future renovations
A vacation property is an asset that can spark emotional and financial tension. Without structure and communication, even the best intentions can lead to disputes.
Develop a well-structured succession plan
A well-structured succession plan takes into account the emotional aspects, family dynamics, practical considerations, and family values. Depending on your family situation, options may include
- Gifting the cottage during your lifetime, ideally with a written agreement
- Establishing a co-ownership or co-tenancy agreement outlining decision-making, scheduling, funding, and exit strategies
- Creating a trust to own the property, which can add a layer of protection and flexibility
- Selling the property, either now or in your will, with proceeds split among beneficiaries
- Equalizing the estate so that one child inherits the vacation property and others receive an equivalent value
These strategies are best explored in collaboration with professional advisors, particularly those with expertise in legal, tax, and estate planning. A well-structured plan reflects your intentions, reduces the risk of future conflict, and helps preserve both the property and your family’s harmony.
Start with a family meeting
Every plan begins with a conversation. We encourage families to hold a structured meeting, ideally with a neutral third party, to ensure everyone has a chance to share their wishes, concerns, and perspectives.
One family we worked with had three adult children. One spent summers at the cottage and felt a deep connection to it. Another visited occasionally for holidays. The third, while grateful for the memories, felt little attachment to the property. The parents had always assumed they would leave the cottage equally to all three, but had never asked what their children wanted.
When the family finally gathered for an open-hearted discussion, everything changed. They listened to one another, shared stories, and reflected on what the cottage truly meant to each of them. It became clear that only one child wished to carry on the legacy. They revised their estate plan, ensuring the other siblings received equal value in different ways, while the one who loved the cottage could continue to enjoy it.
No one felt excluded. In fact, the process brought the family closer. With clarity came relief, and with understanding came peace.
These conversations are not always easy. But when approached with care, they can be a powerful way to honour your legacy, preserve family harmony, and protect what matters most.
A vacation property is a legacy. Protect it.
It’s easy to put off planning. Life is busy. Conversations about death or money are uncomfortable. But the cost of inaction is too great. Without a plan, your family’s most cherished place of connection can become a source of division.
Take the next step
If you or your parents own a cottage or vacation home, now is the time to start the conversation. As Family Wealth Advisors, we are here to guide you through the planning process with care and expertise, helping you preserve your family’s legacy both financially and emotionally.
Let us help you create a plan that protects what matters most and keeps your family connected for generations to come.
Tiffany Harding
Head of Wealth & Estate Planning Services, Family Wealth Advisor
CFP, TEP, FEA, CLU
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